44 Oak St, Weston, MA 02493
Property image
Property image
OFF MARKET

$2,551,100

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,369 sqft (on 0.96 acres)

44 Oak St, Weston, MA 02493

Est. Refi. Payment $15,855/mo*
Refinance Your Home
Currently Off Market - Sold Jul 18, 2014 for $907,500

Home Value

Trulia Estimate
$2.55M
Since last month
$200 (0%)
Since last year
Increased$41K (+1.6%)
Since last sale
Increased$2M (+181.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +153% in the last 10 years
MonthEstimated value
2026
September 2026$2.55M
August 2026$2.55M
July 2026$2.6M
June 2026$2.67M
May 2026$2.69M
April 2026$2.69M
March 2026$2.65M
February 2026$2.57M
January 2026$2.53M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
64 Oak St, Weston, MA
0.10
Single-Family Home
$2,750,000
05/28/26
4
5.5
4,930
50 Hubbard Rd, Weston, MA
0.42
Single-Family Home
$2,100,000
10/15/25
4
3.5
3,220
41 Orchard Ave, Weston, MA
0.73
Single-Family Home
$1,380,000
03/20/26
4
2.5
2,473
2 Candleberry Ln, Weston, MA
0.48
Single-Family Home
$3,180,000
04/28/26
4
4
4,979
556 Wellesley St, Weston, MA
1.05
Single-Family Home
$1,710,000
05/18/26
4
2.5
2,596
23 Stonecroft Cir, Weston, MA
0.22
Single-Family Home
$4,250,000
02/13/26
4
6
8,051
157 Oak St, Weston, MA
0.49
Single-Family Home
$3,100,000
06/17/26
4
3
4,403
49 Newton St, Weston, MA
0.90
Single-Family Home
$2,328,000
04/10/26
4
4.5
3,469
56 Ridgeway Rd, Weston, MA
0.57
Single-Family Home
$2,800,000
10/28/25
5
3.5
3,552
8 Blake Rd, Weston, MA
1.01
Single-Family Home
$1,085,000
07/17/26
5
3.5
4,932

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
64 Oak St, Weston, MA 02493
0.10
$2,750,000
4
5.5
4,930
Recently Sold
50 Byron Rd, Weston, MA 02493
0.19
$3,253,800
5
5
5,739
Off Market
25 Byron Rd, Weston, MA 02493
0.23
$3,351,100
5
4.5
5,802
Off Market
23 Stonecroft Cir, Weston, MA 02493
0.22
$4,250,000
4
6
8,051
Recently Sold
346 South Ave, Weston, MA 02493
0.23
$1,915,300
6
5
4,062
Off Market
67 Byron Rd, Weston, MA 02493
0.26
$14,850,000
7
9
18,725
For Sale
17 Hawthorne Ln, Weston, MA 02493
0.28
$2,559,900
4
5
4,495
Off Market
26 Bittersweet Ln, Weston, MA 02493
0.27
$2,583,400
5
4.5
4,846
Off Market
17 Fields Pond Rd, Weston, MA 02493
0.28
$2,181,900
4
2.5
3,093
Off Market
78 Byron Rd, Weston, MA 02493
0.32
$3,206,200
5
5.5
6,770
Off Market
279 South Ave, Weston, MA 02493
0.31
$1,927,400
4
3
3,960
Off Market
35 Bittersweet Ln, Weston, MA 02493
0.35
$1,971,100
3
3.5
3,419
Off Market

Local Information

  • Map ViewExplore the area around 44 Oak St.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1950
0.96 acre lot
2,369 sqft
$1,077/sqft
Garage

About this House

Ryan Wilson, REALTOR- 781-424-6286Ryan@WilsonGroupRE.comwww.BostonCityandSuburbs.comOpen Houses: Friday May 30th & Sunday June 1st, 11:30-1pm...Beautiful colonial in Weston's highly desirable south side!! Location is everything...close to the amazing schools, multiple commuter rail stops, routes 90 & 95 (20 minute drive to Logan Airport), and directly across the street from acres of town trails! Bright eat-in kitchen with large breakfast bar and French doors that open to the screened in porch overlooking the fabulous, flat back yard. Large living room w/ fireplace, library w/ built-ins & French doors, and dining room w/ hardwood floors. Finished basement w/ fireplace, gas heating system, 2 car garage, surround sound, cedar closet in master and plenty of storage/closets throughout. Welcome home!
44 Oak St, Weston, MA 02493 is a 3 bedroom, 3 bathroom, 2,369 sqft single-family home built in 1950. It last sold for $907,500 on Jul 18, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,551,100, with a rent estimate of $5,572/month.

Home Details for 44 Oak St

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Washer
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: ShinglePorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.96 acres

Price and Tax history

DateEventPrice
Jul 18, 2014
Source: N/A
Sold
$907,500
Jun 22, 2014
Source: Agent Provided
Pending
$935,000
May 29, 2014
Source: Agent Provided
Listed For Sale
$935,000
Dec 29, 1992
Source: N/A
Sold
$298,000

Market trends in Weston

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
48
9MoM

Around this home

What Locals Say about Weston

At least 28 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 85 % Say it's dog friendly

  • 82 % Say it's quiet

  • 80 % Say parking is easy

  • 77 % Say people would walk alone at night

  • 76 % Say there's holiday spirit

  • 74 % Say they plan to stay for at least 5 years

  • 73 % Say yards are well-kept

  • 71 % Say there's wildlife

  • 52 % Say kids play outside

  • 50 % Say neighbors are friendly

  • 44 % Say there are community events

  • 38 % Say there are sidewalks

  • 33 % Say it's walkable to grocery stores

  • 29 % Say streets are well-lit

  • 26 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Woman
    "It’s a Commuter’s dream. 3 minutes to the Pike or 128, Rt. 30, 20, or 9. 2 acres tucked in. Very convenient & private. "
    0
    Flag
  • marc
    "I like in particular the BBQ in the June/July timeframe. Many events are also organized with different themes such as the old,car’,contest."
    3
    Flag
  • Marc
    "Some nice trails to take your dog along with easy access. Plenty of space in the center of town too where you can do long walks. Many people have them which is a plus. "
    0
    Flag
  • Marc d. g.
    "Commute is rather easy since I work in waltham. Best time is to go to work either at 7am or after 9am. The return to home is usually a bit crowded in the 4-6 window but alternative roads exist."
    1
    Flag
  • suez
    "Weston is perfect for families. Excellent schools and this area is a true neighborhood of the old style. Houses are spaced far apart but connected by trials in the abundant conservation land. The neighbors are connected by a love of privacy and nature. They have specifically sought out an area close to Boston that still feels like you are in rural Massachusetts. A mix of historic homes and new modern works well , and the community is united by a love of this very unique environment. We are close to all the amenities of a city yet a world away. You will have to drive to restaurants and shopping and there is no public transportation but you will not have to pack up and vacation in NH or VT, you will live that life everyday and still be 25 minutes from downtown Boston."
    0
    Flag
  • frkmus
    "Open land, a community playground for all homeowners on Kendal Common Rd. and Ellis Rd., allows children to play free of traffic in their virtually private domain. With 20 homes on 40 acres, all constructed in the 1950's, all designed by three architects, this area is unique for many reasons, not the least of which the total absence of fences has for over sixty years firmly implanted a communal spirit among all participating homeowners. The entire land mass is away from main thoroughfares on two virtually private roads; a special haven for young and old alike. Here is where we live and brought up our children."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 44 Oak St

  • What is 44 Oak St estimated to be worth?
    Trulia's estimated value for 44 Oak St in Weston, MA is $2,551,100.
  • What is the price history for 44 Oak St?
    44 Oak St in Weston, MA last sold for $907,500 in July 2014.
  • Is Weston a buyer's or seller's market?
    Weston is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Weston?
    Residents describe Weston, MA as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Weston, MA.
  • How big is the lot at 44 Oak St?
    The lot at 44 Oak St in Weston, MA is about 0.96 acres (41,817 sq ft).
  • Does 44 Oak St have a garage?
    Yes, 44 Oak St in Weston, MA has a garage.

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